Evidence map›Paper›PMID 34987174›Full record

ArticleNature chemistry2022

Decarboxylative cross-nucleophile coupling via ligand-to-metal charge transfer photoexcitation of Cu(II) carboxylates.

Qi Yukki Li, Samuel N Gockel, Grace A Lutovsky, Kimberly S DeGlopper, Neil J Baldwin, Mark W Bundesmann, Joseph W Tucker, Scott W Bagley, Tehshik P Yoon

Open access · greenAbstract read
In one paragraph

Article in Nature chemistry, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 65 papers.

0numbers the graph read from it
0cells of the map it votes in
65citing papers in PubMed
22.4field-weighted citation impact, top 1% of its field
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

65 citing papers in PubMed, 211 citations in OpenAlex.

  1. Article
  2. Article
  3. Article
  4. Review
  5. Article
  6. Article
  7. Enantioconvergent Chan-Evans-Lam C(spJournal of the American Chemical Society · 2026
    Article
  8. Article
  9. Article
  10. Article
  11. Article
  12. Article
  13. Review
  14. Photoexcited LMCT of CuNature communications · 2025
    Article
  15. Ligand-to-Metal Charge Transfer of Ag(II) CFAngewandte Chemie (International ed. in English) · 2025
    Article
  16. Article
  17. Article
  18. Article
  19. Article
  20. Article

5 more citing papers are in PubMed but not listed here.

4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

9 authors at 2 institutions in 1 country.

Qi Yukki Li *Department of Chemistry, University of Wisconsin-Madison, Madison, WI, USA.
Samuel N Gockel *Department of Chemistry, University of Wisconsin-Madison, Madison, WI, USA.
Grace A LutovskyDepartment of Chemistry, University of Wisconsin-Madison, Madison, WI, USA.
Kimberly S DeGlopperDepartment of Chemistry, University of Wisconsin-Madison, Madison, WI, USA.
Neil J BaldwinMedicine Design, Pfizer Inc, Groton, CT, USA.
Mark W BundesmannMedicine Design, Pfizer Inc, Groton, CT, USA.ORCID http://orcid.org/0000-0003-1705-3793
Joseph W TuckerMedicine Design, Pfizer Inc, Groton, CT, USA.
Scott W BagleyMedicine Design, Pfizer Inc, Groton, CT, USA.ORCID http://orcid.org/0000-0002-7365-7332
Tehshik P YoonDepartment of Chemistry, University of Wisconsin-Madison, Madison, WI, USA. tyoon@chem.wisc.edu.ORCID http://orcid.org/0000-0002-3934-4973
University of Wisconsin–Madison · USPfizer (United States) · US

Funding

Visible Light PhotocatalysisR01GM095666 · NIGMS · UNIVERSITY OF WISCONSIN-MADISON · PI YOON, TEHSHIK P · 2011 to 2022
$4.2M
Laser-Enhanced NMR Instrumentation for Chemical and Biochemical ResearchS10OD012245 · OD · UNIVERSITY OF WISCONSIN-MADISON · PI CAVAGNERO, SILVIA · 2013 to 2013
$1.0M
Enabling Triplet-Energy Transfer via NHC CatalysisF32GM139373 · NIGMS · UNIVERSITY OF WISCONSIN-MADISON · PI GOCKEL, SAMUEL N · 2021 to 2022
$87k
NIGMS NIH HHS F32 GM139373NIGMS NIH HHS R01 GM095666NIH HHS S10 OD012245
6 · The paper itself

Abstract

Reactions that enable carbon-nitrogen, carbon-oxygen and carbon-carbon bond formation lie at the heart of synthetic chemistry. However, substrate prefunctionalization is often needed to effect such transformations without forcing reaction conditions. The development of direct coupling methods for abundant feedstock chemicals is therefore highly desirable for the rapid construction of complex molecular scaffolds. Here we report a copper-mediated, net-oxidative decarboxylative coupling of carboxylic acids with diverse nucleophiles under visible-light irradiation. Preliminary mechanistic studies suggest that the relevant chromophore in this reaction is a Cu(II) carboxylate species assembled in situ. We propose that visible-light excitation to a ligand-to-metal charge transfer (LMCT) state results in a radical decarboxylation process that initiates the oxidative cross-coupling. The reaction is applicable to a wide variety of coupling partners, including complex drug molecules, suggesting that this strategy for cross-nucleophile coupling would facilitate rapid compound library synthesis for the discovery of new pharmaceutical agents.

Indexed as

LightCarboxylic AcidsCopperLigandsOxidation-ReductionCarboxylic AcidsCopperLigands

Identifiers

PMID34987174
PMCPMC8820273
OpenAlexW4205478521

What OpenQuestion holds

Textmetadata
LicenceTDM
Read underepoch 390

Registered trials

None linked

Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.